1-(2-(Phenyl-lower-alkyl)-aziridines munition payload

ABSTRACT

A munition having a payload of 1-(2-(3,4,5trimethoxyphenyl)ethyl)aziridine, 1-(1-(3,4,5-trimethoxyphenyl)2-propyl)aziridine and 1-(1(2-methoxy-4,5-methylenedioxyphenyl)2-propyl)aziridine are prepared from the appropriate vinylsubstituted benzene and ethylenimine.

States tent [1 1 Razdan 1 June 17, 1975 1 l-(2-(PHENYL-LOWER-ALKYL)- [56] References Cited AZIRIDINES MUNITION PAYLOAD UNITED STATES PATENTS Inventor: j Razdan, m nt, Mass. 2,654,737 10/1953 Bestian 260/239 Assigneez The United States of America as 3,352,238 1l/1967 Spragg et a1. 102/39 represented by the Secretary of the Army, Washington, DC Przmary Exammer-Ben am1n A. Borchelt Assistant Examiner-Harold Tudor Flledi g- 7, 1971 Attorney, Agent, or Firm-Robert P. Gibson; Nathan [21 Appl. No.1 172,597 Edelberg I t d A l' D t 'HReae US pplcatlon aa ABSTRACT [60] Dwrsron of Ser. No. 22,668, March 25, 1970, Pat.

NO. 3,637,662, which is a continuation-in-part ofSer. A munmon havmg a p y of I No. 640,815, May 24, 1967. trimethoxypher'xyUethyl]aziridine, l-[ -(3,4,5-

trimethoxyphenyl)-2-propy1]aziridine and l-[ 1(2- [52] US. Cl 102/90; 102/66 methoxy-4,S-mthylenedioxyphenyl)-2- [51] Int. Cl. F42b 11/24 propy1]aziridine are prepared from the appropriate vi- [58] Field of Search 102/24, 39, 90, 66; nyl-substituted benzene and ethylenimine. 260/239 4 Claims, No Drawings l-(Z-PHENYL-LOWER-ALKYL)-AZIRIDINES MUNITION PAYLOAD DEDICATORY CLAUSE The invention described herein may be manufacture, used, and licensed by or for the government purposes with the payment to me of any royalty thereon.

This application is a divisional application of my pending US. Pat. Application Ser. No. 22,668 filed Mar. 25, 1970, now US. Pat. No. 3,637,662 continuation-in-part of US. Pat. Application Ser. No. 640,815 filed May 24, 1967, and relates to novel aziridines as a chemical munition payload. More particularly, the invention here is to certain 2-(tri-substituted phenyl)ethylaziridines as ther munition payload.

The aziridines of the invention, have in the free base form the structural formulas and wherein R is hydrogen or methyl.

compounds as therapeutic agents and other prior art compounds as lethal or incapacitating agents. The nature of the functional groups of the compounds, the length and branching of aliphatic chains, and the number and configuration of aromatic and alicyclic rings affect the case or difficulty of approach of the compound to the specific neuromuscular junctions and other acetylcholine receptive sites. Substitution of different functional groups influence association and hydration and can considerably change the solubilities in animal physiological media, either in vivo or in vitro.

As demonstrated by the test data set forth in Table l, the compounds of this invention are mildly toxic, and, due to the toxicity, the compounds of this invention interfere with the normal process of neuromuscular impulse transmission and disrupt the propagation of impulses from animal nerves to muscles and mildly incapacitate the animal. Accordingly, the compounds of my invention were conceived and reduced to practice to supply a long sought composition which, due to abnormal physiological behavior produced in animals as a result of the effect on the central nervous system caused by the toxicity of the compound, can be used as an agent to induce mild incapacitation in an animal. The abnormal physiological behavior can result from mere contact of the compounds of this invention with the skin of the animal, and such contact can be brought about by means of dissemination of the compound by any conventional chemical munition having the compounds of this invention as a payload such as bombs, shells, spray tanks, rockets, missiles, aerosol generatirs, etc.

The principal object of this invention is to utilized as the payload in a chemical munition a new composition of matter useful to induce incapacitation in an animal.

Other objects of and uses for my invention will be obvious from and will appear hereinafter in the following detailed description of the invention.

TABLE I Dose/Animal Screen Animal Compound Tested Weight In mg/kg Symptoms Example I end product herein Example ll end product herein LD dosage necessary to kill MEDSO dosage necessary to incapacitate The preparation of the new 2-(trisubstitutedphenyl)-ethylaziridines is carried out by treating the appropriately substituted vinylbenzene with ethylenimine in the presence of sodium metal. Conveniently the substituted phenyl alkene is interacted with an excess of ethylenimine as a solvent to produce the aziridines. The free base can be isolated as such or converted to any desired acid addition salt by treatment with one equivalent of the appropriate organic or inorganic acid. The acid addition salts of the base are the form in which the base is more conveniently prepared for use and are the full equivalents of the subject matter specifically claimed.

The intermediate vinylbenzenes are a known class of compounds generally prepared by dehydration of the EXAMPLE 1 l-[2-( 3 ,4,5-Trimethoxyphenyl )ethyl]aziridine ether layer was washed with water, dried and the ether removed by evaporation. Fractional distillation gave 1.72 g. of l-[2(3,4,5-trimethoxy)-ethyl]aziridine, b.p.

EXAMPLE 2 l l-( 3 ,4,5-Trimethoxyphenyl)-2-propyl]aziridine was prepared from 6 g. of l-(3,4,5-trimethoxyphenyl)- l-propene and 0.13 g. of sodium-metal in 3 ml. of

ethylenimine using the procedure described in Example 1. There was thus obtained 2.1 g. of l-[1-(3,4,5- trimethoxyphenyl)-2-propyl]aziridine, b.p. lOO10l/0.4 mm.

EXAMPLE 3 l-[ l-(2-Methoxy-4,5-methylenedioxyphenyl)-2- propyl)-aziridine was prepared was prepared from 7 g. of l-( 2-methoxy-4,5-methylene-dioxyphenyl l propene, 0.9 g. of atomized sodium in 9 ml. of ethylenimine using the procedure described in Example 1. The 1-[ l-(2-methoxy-4,S-methylenedioxyphenyl)-2- propyl]aziridine thus obtained had the b.p. lOl/O.3 55

CH 0 .CH2CHNQ OR CH 2 o Intermediates I l-(3,4,5 Trimethoxyphenyl)ethanol A solution of 25 g. of 3,4,5-trimethoxybenzaldehyde in 720 ml. of ether was added to a refluxing solution of methylmagnesium bromide made from 6.22 g. of magnesium turnings and 25.26 g. of methyl bromide in 400 ml. of ether. The mixture was refluxed for 12 hours then hydrolyzed with 300 ml. of 10% ammonium chloride. The ether layer was separated, the aqueous layer extracted with ether and the combined extracts washed with water and dried. The ether was removed by evaporation and the residue fractionally distilled to give 2l g. of 1(3,4,5-trimethoxyphenyl)ethanol, b.p.

l33l34/0.l mm.

3 ,4,5-Trimethoxystyrene The 1-(3,4,5-trimethoxyphenyl)ethanol prepared as above 14.6 g.) was added dropwise to 2.5 g. of freshly fused potassium hydrogen sulfate, containing a small crystal of p-t-butyl-catechol, at 220-230, while the pressure was kept at 18 mm. After the addition was complete the temperature and pressure were held constant for 10 minutes, then the pressure was slowly lowered and the product distilled at 0.2 mm. The distillate was dissolved in 50 ml. of ether, the ether solution washed with water and dried, and a small amount of tbutylcatichol added. After the ether was removed by distillation the residue was fractionated to give 5.8 g. of 3,4,5-trimethoxystyrene, b.p. 99-lOl/0.5 mm.

It is obvious that other modifications may be made of my invention, and I desire that my invention be limited only by thescope of the appended claims.

What is claimed is:

l. A munition comprising: a means for delivery, and a payload, said payload comprising a compound of the formula R l CHN C H wherein R is hydrogen or methyl.

2. A compound according to claim 1 of formula (A) wherein R is hydrogen.

3. A compound according to claim 1 of Formula (A) wherein R is methyl.

4. A compound according to claim 1 of Formula (B) wherein R is methyl. 

1. A MUNITION COMPRISING: A MEANS FOR DELIVERY, AND A PAYLOAD, SAID PAYLOAD COMPRISING A COMPOUND OF THE FORMULA
 2. A compound according to claim 1 of formula (A) wherein R is hydrogen.
 3. A compound according to claim 1 of Formula (A) wherein R is methyl.
 4. A compound according to claim 1 of Formula (B) wherein R is methyl. 